The Mad Men Bar Crawl

At first sight, my ‘adventure’ probably seems far less adventurous than others in this issue. In practice, though, I think mine edges the others in terms of risking personal health and safety. I’m in New York for a Mad Men-inspired bar crawl. Essentially, I’m playing a live-action drinking game based on one of the most booze-fuelled TV shows in history. In the first season, Roger tells Don, “We drink because it’s what men do.”

This is the mantra I will live by. Of course, three episodes later, Roger’s adherence to this mantra sees him violently regurgitate half-digested oysters on to the shoes of some prospective clients, but that’s a risk I am prepared to take in the name of journalism.

Old fashioneds at the Mark

Since most Mad Men drinking takes place during working hours, my pilgrimage begins at midday on a Thursday. I travel along the eastern outskirts of Central Park to The Mark Bar; a swanky cocktail lounge where today’s Dons and Rogers talk shop over high-quality liquor. I order Don’s favourite, an old fashioned – here made with sour cherry as its bass note – followed swiftly by another one, before staggering across the road to Bar Pleiades on E76 St.

The interior of the Mark Bar

Martinis and oysters

I feel I should honour Roger now, so I order oysters and martini. In moderation – one martini and one plate of oysters – the mixture works well; the oysters’ sea-salt freshness provides a counterpoint to the martini’s tang. I bump into some sharply-dressed financiers on a decadent “business” lunch, who point me in the direction of a place nearby called the Monkey Bar which, they say, is thronging with “guys in $3,000 suits”. Google Maps describes the Monkey Bar as a “power restaurant” – worth a visit.

A meaner mojito

Before that, I head to Bemelmans – a Thirties piano bar. The piano has recently received tinkling from Paul McCartney and Bono (but don’t let that put you off), and Woody Allen plays jazz clarinet at its sister venue, Café Carlyle. Drink-wise, I plump for an old Cuban (rum, Angostura bitters, lime juice, mint, Canard-Duchêne champagne) – the louder, bawdier cousin of the mojito. When the barman asks if I’d like another, I crowbar in a classic Sterling-ism from Season 6, telling him, “Don’t let me see the bottom of this glass.” He responds by handing me a coaster, which gets a big laugh from the pianist, and makes me realise I should just channel Roger non-verbally from now on.

Tom suited and sipping an old fashioned - Don Draper lives on

Stopping at Don’s

Having sunk two old Cubans, I stumble across to the Roosevelt Hotel; a Mad Men landmark as this is where Don comes to live, like an upmarket Alan Partridge, after Betty chucks him out in Season 2. Fittingly, the man next to me at the bar immediately rattles off an uninvited monologue about his ex-wife, tinged with a bitterness that rivals my old fashioned.

An absinthe ending

It should very much be home time, but there’s still the Monkey Bar to inspect. Inspired by an ‘eccentric’ Twenties starlet who drank here with her pet chimps, the walls are adorned with utterly mad murals of cartoon monkeys; cigar-chomping simians in suits gurning down at you in the smoky light. The bar’s signature Monkey Gland cocktail (gin, pomegranate molasses, orange juice, Absinthe) is the best I sample all night, as it tastes like an exact cross between Fruit Salads and Black Jacks.The barman asks if I fancy one more, which I do, but I notice that the place has emptied. So, with Roger’s other mantra – “They say once you start drinking alone, you’re an alcoholic” – ringing, I wobble home to bed.

The Details

Fly: British Airways flies to New York from £639 including tax and charges. BA’s exclusive 32-seat all-business class jet flies from London City airport to JFK 10 times a week, from £2,704; ba.com

Stay: Don Draper-style sophistication and luxury can be found at Viceroy New York, 120 W 57th Street New York, NY 10019; viceroyhotelsandresorts.com